O. Yale Lewis sits behind the desk in his downtown, 41st-floor corner office at the Hendricks & Lewis law firm and points to several framed documents on the wall. In his affable Alabama drawl, he explains that they come from his representation of Al Hendrix, Jimi Hendrix’s father. One of the documents, a 1993 letter from opposing counsel, pithily summarizes the stakes of that case: “The damages actually incurred by my clients will exceed, substantially, the policy limits of any insurance coverage you or your client may have.” In other words, if Lewis were to lose (he and his firm were later named as defendants in a countersuit), he would be financially ruined.

As you might have guessed from his top-floor digs, Lewis did not lose. Instead, he secured Al Hendrix’s rights to his son’s catalog, a success that brought more high-profile clients, often referred to him by newspaper and magazine reporters. The new clientele shifted Lewis’ practice from an emphasis on land-use issues to that rare breed: the entertainment law firm not located in Los Angeles, New York City, or Nashville.

In the first phase of his career, Lewis helped design and run public development authorities for Pioneer Square and Pike Place Market, litigated aboriginal rights in land disputes, served as general counsel for a shipbuilding company, and even provided legal advice to Seattle Weekly. But since the Hendrix case, he has represented, among others, Courtney Love and Frances Bean Cobain; the family of Buddy Holly; syndicated radio personality Delilah; and Johnny Mulhair, who produced the album that made LeAnn Rimes famous. (Lewis notes that the entire office works together on cases, but he tends to be the lead attorney for the music clients, while his partner, Kate Hendricks, works more often with publishers, playwrights, and photographers.)

Sometime in the next month, Lewis will be flying to Los Angeles to represent Dr. Funkenstein himself, George Clinton, in a federal trial against Capitol Records and Priority Records. The trial is one of two Clinton has scheduled against Capitol and its subsidiaries; a third trial, against Universal Music Group, is slated for July. A federal judge has ruled that Capitol infringed on Clinton’s copyrights to the Funkadelic masters (consisting of the albums Hardcore Jollies, One Nation Under a Groove, Uncle Jam Wants You, and The Electric Spanking of War Babies) when it released them in 1993 and again in 2002; all that remains at trial is to determine Clinton’s damages.

Additionally, Clinton is suing for royalties from Capitol’s and Universal’s sampling and other use of his recordings, and, in a somewhat novel argument, contending that Capitol breached its fiduciary duty to him. This is significant because the claim is based on an understanding of the artist’s relationship with his label as a “joint venture” rather than as a simple contract for services. Legally, joint venturers have much higher obligations to deal ethically and transparently with one another; should Clinton succeed, it could have significant effects throughout the industry, lessening the power advantage labels have over their artists.

While hip-hop aficionados debate whether Clinton has surpassed James Brown as the genre’s most sampled artist, there’s no question that he hasn’t seen the riches he might expect from having his hooks underpin the success of some of the best-selling rap acts of the 1980s and ’90s. (Though Clinton has regained control over the Funkadelic masters, the publishing rights to much of his work remain in the possession of Bridgestone Music, a company headed by a man named Armen Boladian, whom Clinton accuses of having stolen rights through altered contracts and forged signatures.) Say what you will about Dr. Dre’s production skills, he wouldn’t be filthy rich and a household name if it weren’t for George Clinton hooks. His early-’90s “G-Funk” sound (a pun on Clinton’s ’70s Parliament-Funkadelic, or “P-Funk,” sound) led to multiplatinum sales for his debut solo album, The Chronic, and Snoop Doggy Dogg’s solo debut, Doggystyle. Hit singles like “Fuck wit Dre Day,” “Who Am I (What’s My Name)?,” and “Let Me Ride” borrowed their hooks from Clinton grooves like “Atomic Dog” and “Swing Down, Sweet Chariot.” With these cases, Clinton hopes finally to begin to get his.

Right now, though, Lewis is telling the story of the Hendrix case and the seemingly bottomless rabbit hole of offshore companies through which, court documents show, Leo Branton Jr., the lawyer looking to sell the Hendrix catalog, hid money and transferred ownership rights. Lewis stumbled into the case when Janie Hendrix, Al’s adopted daughter, asked him to review a contract by which she would sell part of her interest in the catalog.

Lewis thought that contract and some of the others that had been suggested to Al and Janie looked suspicious, but he didn’t grasp the magnitude of the problem until he received a phone call from Chuck Philips of the Los Angeles Times, informing him of Branton’s plans to sell the entire catalog to Universal. “There was going to be a big bonanza in New York City to announce the acquisition,” says Lewis. “Press were flying in from around the world.” Knowing he had to move quickly, he exchanged letters with Branton’s counsel and won the race to the courthouse, filing his suit on Friday afternoon while Branton’s countersuit wasn’t filed until Monday morning.

For a while, Al had a $5 million pledge for legal fees from Paul Allen, who was himself interested in acquiring the catalog. Allen’s potential financial backing did little to assuage Lewis’ anxiety over the case’s potentially disastrous financial consequences, something he says he worried about every day. Explains Lewis, “When you have a bacon-and-egg breakfast, the chicken is involved, but the pig is committed. We were committed to this litigation before Paul Allen was involved.” (Allen and Al later had a falling-out, one reason the current Experience Music Project is not exclusively a Hendrix museum.)

The big break came in the form of an anonymous phone call from a U.S. attorney. “He said he was a big Jimi Hendrix fan,” explains Lewis, “and that he was calling from a pay phone so it couldn’t be traced.” This deep throat informed Lewis that, as part of its tax fraud investigation of entertainment lawyer Harry Margolis, the Justice Department had seized and converted to microfiche a huge number of documents relating to the Hendrix case from a warehouse behind the Ample Hamper delicatessen in the Virgin Islands.

“We staffed up massively,” says Lewis. “We had 14 lawyers, and we bought a microfiche machine and had people reading the documents around the clock. It was really tedious labor.” The case lasted more than two years, and though the settlement marked the end of Lewis’ involvement in Hendrix affairs, the family continued to battle over Jimi’s legacy, with Janie ultimately winning the rights to the estate over Jimi’s brother Leon.

That Lewis received a tip from a devoted Hendrix fan is telling: His work constantly puts him in contact with artists about whom millions are passionate. A recent perk occurred during a business trip to Detroit. He and George Clinton were in a hotel lounge when the house jazz band recognized Clinton and invited him onstage. After a halfhearted protestation, Clinton accepted, performing “his whole repertoire,” says Lewis. As word of the performance spread, the lounge quickly went from mostly empty to overflowing.

Lewis says he found the performance, and the circumstances leading up to it, “absolutely stunning,” but he concedes that he likely didn’t enjoy it as much as many others did. (Lewis also received neckties as gifts from Clinton, who told him the subdued ones are “from Parliament,” the flamboyant ones “from Funkadelic.”) His primary interest is in the legal issues. “It’s nothing I would’ve envisioned,” he says of representing entertainers. “It came from following my interest in intellectual property issues. I remain largely uninitiated in the ways of the entertainment world.” His clients find this amusing. “I remember one time, I got a call from Courtney Love,” whom he represented along with her daughter, Frances Bean Cobain, in their successful lawsuit for control over the Cobain legacy, and with whom his firm recently settled a fee dispute. “She said, ‘Last night, there was this big event that’s very important to people in the industry. It’s called the Grammys.'”

Terri Williamson, who became a Lewis client partly on Love’s recommendation, confirms Lewis’ lack of familiarity with the entertainment world. “Clueless might be an understatement,” she says. “But [his ignorance] is endearing.” And, she notes, he immerses himself in industry details for his cases, as he did when he represented her and her corporation, Glow Industries, in a trademark infringement lawsuit against Jennifer Lopez for the star’s Glow by J.Lo perfume.

“From the beginning, he really took the time to understand what I do,” Williamson explains, adding that he was the first lawyer she had dealt with who had done so. “He asked me to do a primer on the beauty industry for him. He went from ‘I know there’s soap and shaving cream out there and I use them’ to a complex understanding of market size and product niches.” Lewis’ understanding evolved to the point where Williamson, who has an MBA from the University of Chicago and nearly a decade of consulting experience, now views him as a business adviser. “There have been opportunities that have come my way in the past year where my initial reaction has been caution or dismissal. Then, when I run them by Yale, he sees the opportunities that I missed.”

While the cases keep rolling in, none has been as high-stakes as the Hendrix catalog dispute. Asked whether he would take on a case like that again, Lewis says, “Not voluntarily. I learned a lot, so I suppose it would be easier the second time. But then, I wouldn’t learn as much.” He pauses for a second. “No, I certainly would not do that again.”